A kind of tert-butylaminoethoxyethanol, its derivatives and catalytic synthesis method
By using ternary eutectic solvents as catalysts in tubular reactors, the equipment corrosion, long reaction time, high economic cost and low selectivity in the synthesis of tert-butylamine ethoxyethanol and its derivatives in the prior art is solved. The problem of this paper has achieved an efficient and economical preparation method, and the product yield and purity have been significantly improved.
Patent Information
- Application Number
- CN202410492679.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2024-04-23
- Publication Date
- 2025-02-07
- Estimated Expiration
- 2044-04-23
AI Technical Summary
The method for synthesizing tert-butylamine ethoxyethanol and its derivatives in the prior art has problems such as severe equipment corrosion, long reaction time, high economic cost and low selectivity.
Tertiary eutectic solvents are used as catalysts to synthesize tert-butylamine ethoxyethanol and its derivatives in a tubular reactor, and the catalyst is prepared by simple mixing, heating and vacuum drying.
The yield and purity of the product is significantly improved, with the maximum yield up to 95%, and the purity of the product is above 98%, reducing economic costs and simplifying the process.
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Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of organic compound synthesis, and particularly relates to tert-butylaminoethoxyethanol, its derivatives and a catalytic synthesis method. Background Art
[0002] Tert-butylaminoethoxyethanol is a transparent, colorless liquid with a special ammonia smell, which can be dissolved in most organic solvents such as ethanol, ether and ketone. The structure of tert-butylaminoethoxyethanol contains a large tert-butyl group (steric coefficient is 1.74). The tert-butyl group is connected to the nitrogen atom on the amino group, which makes tert-butylaminoethoxyethanol have a highly efficient steric hindrance effect, and its steric hindrance constant value reaches 2.10. The strong steric hindrance effect of the tert-butyl group can not only inhibit the reaction with CO2 to a limited extent, but also significantly increase the alkalinity of the solution and enhance the ability to selectively absorb H2S. At present, tert-butylaminoethoxyethanol is widely used in the fields of selective desulfurization solvents in oil refineries and natural gas purification plants. Under the same process conditions, compared with methyldiethanolamine, tert-butylaminoethoxyethanol has more than 3 times the selectivity for H2S, and the energy consumption required is only about 70% of that of methyldiethanolamine. At the same time, by introducing different functional groups to modify tert-butylaminoethoxyethanol, a variety of tert-butylaminoethoxyethanol derivatives can be obtained, which are widely used in organic synthesis, medicinal chemistry, dye chemistry, catalytic chemical surfactants, and ionic liquid precursors. Therefore, the synthesis research of tert-butylaminoethoxyethanol and its derivatives is of great research value and industrial application significance.
[0003] At present, the synthesis methods of tert-butylaminoethoxyethanol and its derivatives are mainly tert-butylamine and diethylene glycol method and tert-butylamine and halogenated alkyl alcohol method. Among them, the reaction of tert-butylamine and diethylene glycol method requires the use of metal catalysts prepared by active components such as Ni, Co, Ru and Cu. U.S. Patent US4487967A reported that a supported catalyst prepared by loading Ni as the main active component on Al2O3-SiO2 carrier was used for the reaction of diethylene glycol and tert-butylamine to prepare tert-butylaminoethoxyethanol. The research results showed that under the conditions of Ni loading of 65wt%, reaction temperature of 200℃ and reaction time of 6h, the yield of tert-butylaminoethoxyethanol was 54%; however, the process has the disadvantages of serious loss of active components and low atomic utilization of active component Ni. Chinese patent CN108906061A prepared Ni-based catalysts with different carriers by isovolumetric impregnation method and studied its catalytic performance for diethylene glycol and tert-butylamine. The research results show that under the action of Ni-based catalyst supported by SiO2, the conversion rate of diethylene glycol and the selectivity of tert-butylaminoethoxyethanol are 49.4% and 83.3% respectively under the optimal process conditions, but there are also problems such as high reaction pressure and long reaction time. The method for preparing tert-butylaminoethoxyethanol by reacting tert-butylamine with halogenated alkyl alcohol in a reactor without catalyst heating and self-pressure conditions disclosed in Chinese patent CN1623978A has a long reaction time, high reaction temperature and serious equipment corrosion, which increases the economic cost of production.
[0004] Low eutectic solvents are a new type of green ionic liquid analogue proposed in the early 21st century. Low eutectic solvents have easy-to-obtain raw materials, simple preparation processes, are non-toxic and biodegradable, and are widely used in organic synthesis, catalytic chemistry, and materials chemistry. Especially in the field of catalytic chemistry, low eutectic solvents have the advantages of high catalytic efficiency and mild conditions, and have shown great application prospects in related fields. Tubular reactors have low back mixing and high volumetric efficiency. For processes with cascade side reactions, they can improve their selectivity and reduce the generation of by-products.
[0005] In summary, the current methods for synthesizing tert-butylaminoethoxyethanol and its derivatives include the diethylene glycol and tert-butylamine method, which has the problems of large amount of supported catalyst metal active components, high reaction temperature and pressure, and severe equipment corrosion, long reaction time, high economic cost and low selectivity under the condition of no catalyst in the halogenated alkyl alcohol and tert-butylamine method. In view of this, the synthesis of tert-butylaminoethoxyethanol and its derivatives in a tubular reactor using a ternary deep eutectic solvent as a catalyst is an efficient and economical preparation method. Summary of the invention
[0006] In view of the above-mentioned deficiencies in the prior art, the present invention provides a tert-butylaminoethoxyethanol, its derivatives and a catalytic synthesis method, which can effectively solve the problems of severe equipment corrosion, long reaction time, high economic cost and low selectivity in the process of synthesizing tert-butylaminoethoxyethanol and its derivatives by using a haloalkyl alcohol and tert-butylamine method, and provides a preparation method for tert-butylaminoethoxyethanol and its derivatives. The method has a simple catalyst preparation process, a small amount of catalyst, a short reaction time in a tubular reactor, high selectivity, and a maximum yield of tert-butylaminoethoxyethanol and its derivatives of up to 95%, and a product purity of more than 98%.
[0007] To achieve the above purpose, the technical solution adopted by the present invention to solve the technical problem is:
[0008] A method for catalytically synthesizing tert-butylaminoethoxyethanol and its derivatives, wherein a ternary low eutectic solvent is used as a catalyst, a reaction medium, a raw material represented by formula I and a raw material represented by formula II are mixed, and the mixture is reacted to obtain the product;
[0009] The structural formula of the raw material shown in Formula I is:
[0010] The structural formula of the raw material shown in Formula II is:
[0011] Among them, R1, R2 and R3 are independently selected from hydrogen atom, methyl, ethyl, propyl, butyl, isopropyl, hydroxyl, carboxyl, methoxy, aldehyde, hydroxymethyl, methyl substituted with 1 to 3 halogen atoms; R4 is selected from chlorine atom, bromine atom, iodine atom or aldehyde group; n is 1 to 6.
[0012] Furthermore, the molar ratio of the raw material represented by formula I to the raw material represented by formula II is 2 to 12:1.
[0013] Furthermore, the molar ratio of the raw material represented by formula I to the raw material represented by formula II is 3 to 7:1.
[0014] Furthermore, the mass ratio of the ternary low eutectic solvent to the raw material represented by formula II is 0.01 to 0.45:1.
[0015] Furthermore, the mass ratio of the ternary low eutectic solvent to the raw material represented by formula II is 0.02 to 0.20:1.
[0016] Furthermore, in the raw material represented by formula I, R1 and R3 are both hydrogen atoms, and R2 is a hydrogen atom or a methyl group.
[0017] Furthermore, in the raw material represented by formula II, R4 is Cl, and n is 1 or 4.
[0018] Furthermore, the synthesis reaction temperature is 55-180° C., the pressure is 0.1-8 MPa, and the time is 30-420 min.
[0019] Furthermore, the synthesis reaction temperature is 75-170° C., the pressure is 0.1-5 MPa, and the reaction time is 40-300 min.
[0020] Furthermore, the preparation method of the ternary low eutectic solvent is: after mixing the hydrogen bond donor and the hydrogen bond acceptor, heating at 50-120° C. for 30-200 min and then vacuum drying to obtain the ternary low eutectic solvent.
[0021] Furthermore, the vacuum drying time is 240 to 360 minutes, and the drying temperature is 40 to 70°C.
[0022] Furthermore, the hydrogen bond donor is selected from one or two of urea, thiourea, acetamide, propionamide, ethanolamine, sodium hydroxide, potassium hydroxide, ethylene glycol, glycerol, and 1,3-propylene glycol.
[0023] Furthermore, the hydrogen bond acceptor is selected from one or two of choline chloride, choline bromide, choline iodide, N-benzyl-2-hydroxy-N,N-dimethylethanolammonium chloride, and N-ethyl-2-hydroxy-N,N-dimethylethanolammonium chloride.
[0024] Further, the ternary low eutectic solvent may include [urea][thiourea][choline chloride], [urea][sodium hydroxide][choline chloride], [sodium hydroxide][ethylene glycol][choline chloride], [urea][choline chloride][choline bromide], [sodium hydroxide][N-ethyl-2-hydroxy-N,N-dimethylethanolammonium chloride][choline chloride], and the like.
[0025] Furthermore, the molar ratio of one or two substances in the hydrogen bond donor to two or one substance in the hydrogen bond acceptor is preferably (0.6-5.5):1:1 and 1:(0.8-5):1, more preferably (1.1-3.8):1:1 and 1:(1.5-3.5):1.
[0026] Furthermore, the reaction medium is one or more of water, methanol, ethanol, propanol, isopropanol, and ethylene glycol, and more preferably one or more of water, methanol, and ethanol.
[0027] A catalytic synthesis of tert-butylaminoethoxyethanol and its derivatives, prepared by the above method, has the following structural formula:
[0028]
[0029] Wherein, R1, R2 and R3 are independently selected from hydrogen atom, methyl, ethyl, propyl, butyl, isopropyl, hydroxyl, carboxyl, methoxy, aldehyde, hydroxymethyl, and methyl substituted with 1 to 3 halogen atoms.
[0030] Beneficial effects of the present invention:
[0031] The present invention provides a preparation method of a ternary low eutectic solvent and a synthesis method of tert-butylaminoethoxyethanol and its derivatives catalytically synthesized in a tubular reactor. The ternary low eutectic solvent is used as a catalyst and reacted in a tubular reactor, effectively solving the problems of severe equipment corrosion, long reaction time, high economic cost and low selectivity under the condition of no catalyst in the halogenated alkyl alcohol and tert-butylamine method. At the same time, the raw material cost of the ternary low eutectic solvent catalyst used in the present invention is low. The preparation process is simple, and the ternary low eutectic solvent catalyst can be obtained by simple mixing, heating and vacuum drying.
[0032] The present invention provides a method for preparing a ternary low eutectic solvent and a method for catalytically synthesizing tert-butylaminoethoxyethanol and its derivatives in a tubular reactor. After acid-base neutralization, rough separation and distillation, the maximum yield can reach 95% (calculated as halogenated alkyl alcohol), and the product purity is higher than 98%, which has certain economy and practicality. DETAILED DESCRIPTION
[0033] The specific implementation modes of the present invention are described below so that those skilled in the art can understand the present invention. However, it should be clear that the present invention is not limited to the scope of the specific implementation modes. For those of ordinary skill in the art, as long as various changes are within the spirit and scope of the present invention as defined and determined by the attached claims, these changes are obvious, and all inventions and creations utilizing the concept of the present invention are protected.
[0034] Example 1
[0035] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0036] First, sodium hydroxide, urea and choline chloride were weighed into a round-bottom flask at a molar ratio of 0.8:1:1, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [urea][sodium hydroxide][choline chloride].
[0037] Subsequently, 223.88 g (3 mol) of tert-butylamine, 127.1 g (1 mol) of dichloroethylene glycol, 2 wt% (calculated as dichloroethylene glycol) of a ternary low eutectic solvent catalyst, and 530 g of reaction medium water were added to the tubular reactor after being fully mixed in a static mixer using metering pumps. The pressure of the tubular reactor was maintained at 0.5 MPa and the temperature was maintained at 80° C. The reaction residence time was controlled to be 50 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation and distillation, and the product yield and purity were 82% and 96%, respectively.
[0038] Example 2
[0039] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0040] First, sodium hydroxide, urea and choline chloride were weighed into a round-bottom flask in a molar ratio of 3:1:1, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [urea][sodium hydroxide][choline chloride].
[0041] Subsequently, 223.88 g (3 mol) of tert-butylamine, 127.1 g (1 mol) of diethylene glycol, 2 wt% (calculated as diethylene glycol) of a ternary low eutectic solvent catalyst, and 530 g of a reaction medium methanol were added to a tubular reactor after being fully mixed in a static mixer using metering pumps. The pressure of the tubular reactor was maintained at 0.5 MPa and the temperature was maintained at 80° C. The reaction residence time was controlled to be 50 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation, and distillation. The product yield and purity were 88% and 96%, respectively.
[0042] Example 3
[0043] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0044] First, sodium hydroxide, urea and choline chloride were weighed into a round-bottom flask in a molar ratio of 4:1:1, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [urea][sodium hydroxide][choline chloride].
[0045] Subsequently, 223.88 g (3 mol) of tert-butylamine, 127.1 g (1 mol) of dichloroethylene glycol, 2 wt% (calculated as dichloroethylene glycol) of a ternary low eutectic solvent catalyst, and 530 g of reaction medium water and methanol were fully mixed in a static mixer in advance and then added to the tubular reactor using metering pumps. The pressure of the tubular reactor was maintained at 0.5 MPa and the temperature was maintained at 80° C. The reaction residence time was controlled to be 50 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation and distillation, and the product yield and purity were 80% and 95%, respectively.
[0046] Example 4
[0047] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0048] First, sodium hydroxide, urea and choline chloride were weighed into a round-bottom flask in a molar ratio of 1:2:1, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [urea][sodium hydroxide][choline chloride].
[0049] Subsequently, 223.88 g (3 mol) of tert-butylamine, 127.1 g (1 mol) of dichloroethylene glycol, 2 wt% (calculated as dichloroethylene glycol) of a ternary low eutectic solvent catalyst, and 530 g of a reaction medium methanol were added to a tubular reactor after being fully mixed in a static mixer using metering pumps. The pressure of the tubular reactor was maintained at 0.5 MPa and the temperature was maintained at 80° C. The reaction residence time was controlled to be 50 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation and distillation, and the product yield and purity were 86% and 96%, respectively.
[0050] Example 5
[0051] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0052] First, sodium hydroxide, acetamide and choline chloride were weighed into a round-bottom flask in a molar ratio of 1:2:1, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [urea][sodium hydroxide][choline chloride].
[0053] Subsequently, 223.88 g (3 mol) of tert-butylamine, 127.1 g (1 mol) of dichloroethylene glycol, 4 wt% (calculated as dichloroethylene glycol) of a ternary low eutectic solvent catalyst, and 530 g of a reaction medium methanol were added to a tubular reactor after being fully mixed in a static mixer using metering pumps. The pressure of the tubular reactor was maintained at 0.8 MPa and the temperature was maintained at 90° C. The reaction residence time was controlled to be 60 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation, and distillation. The product yield and purity were 82% and 95%, respectively.
[0054] Example 6
[0055] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0056] First, sodium hydroxide, ethylene glycol and choline chloride were weighed into a round-bottom flask in a molar ratio of 1:2:3, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [sodium hydroxide][ethylene glycol][choline chloride].
[0057] Subsequently, 223.88 g (3 mol) of tert-butylamine, 127.1 g (1 mol) of dichloroethylene glycol, 4 wt% (calculated as dichloroethylene glycol) of a ternary low eutectic solvent catalyst, and 530 g of a reaction medium methanol were fully mixed in a static mixer and then added to a tubular reactor using metering pumps. The pressure of the tubular reactor was maintained at 1.2 MPa and the temperature was maintained at 100° C. The reaction residence time was controlled to be 90 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation and distillation, and the product yield and purity were 95% and 98%, respectively.
[0058] Example 7
[0059] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0060] First, sodium hydroxide, choline iodide and choline chloride were weighed into a round-bottom flask in a molar ratio of 2:1:1, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [sodium hydroxide][choline iodide][choline chloride].
[0061] Subsequently, 223.88 g (3 mol) of tert-butylamine, 127.1 g (1 mol) of dichloroethylene glycol, 3 wt% (calculated as dichloroethylene glycol) of a ternary low eutectic solvent catalyst, and 530 g of a reaction medium methanol were added to a tubular reactor after being fully mixed in a static mixer using metering pumps. The pressure of the tubular reactor was maintained at 1.6 MPa and the temperature was maintained at 100° C. The reaction residence time was controlled to be 70 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation and distillation, and the product yield and purity were 88% and 96%, respectively.
[0062] Example 8
[0063] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0064] First, sodium hydroxide, ethylene glycol and choline chloride were weighed into a round-bottom flask in a molar ratio of 1:2:3, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [sodium hydroxide][ethylene glycol][choline chloride].
[0065] Subsequently, 223.88 g of tert-butylamine (3 mol), 127.1 g (1 mol) of diethylene glycol, 6 wt% of a ternary low eutectic solvent catalyst (calculated as diethylene glycol), and 530 g of a reaction medium, methanol, were fully mixed in a static mixer and then added to a tubular reactor using metering pumps. The pressure of the tubular reactor was maintained at 1.8 MPa and the temperature was maintained at 100° C. The reaction residence time was controlled to be 90 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation, and distillation. The product yield and purity were 89% and 97%, respectively.
[0066] Example 9
[0067] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0068] First, sodium hydroxide, ethylene glycol and choline chloride were weighed into a round-bottom flask in a molar ratio of 1:2:3, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [sodium hydroxide][ethylene glycol][choline chloride].
[0069] Subsequently, 223.88 g (3 mol) of sec-butylamine, 127.1 g (1 mol) of dichloroethylene glycol, 6 wt% (calculated as dichloroethylene glycol) of a ternary low eutectic solvent catalyst, and 530 g of a reaction medium methanol were added to a tubular reactor after being fully mixed in a static mixer using metering pumps. The pressure of the tubular reactor was maintained at 1.8 MPa and the temperature was maintained at 100° C. The reaction residence time was controlled to be 90 min. Finally, the reaction solution was subjected to acid-base neutralization, crude separation, and distillation. The product yield and purity were 92% and 98%, respectively.
[0070] Example 10
[0071] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0072] First, sodium hydroxide, ethylene glycol and choline chloride were weighed into a round-bottom flask in a molar ratio of 1:2:3, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [sodium hydroxide][ethylene glycol][choline chloride].
[0073] Subsequently, 223.88 g (3 mol) of sec-butylamine, 152.6 g (1 mol) of 5-(2-chloroethoxy)pentanol, 6 wt% (calculated based on 5-(2-chloroethoxy)pentanol) of a ternary low eutectic solvent catalyst, and 530 g of a reaction medium, methanol, were added to a tubular reactor after being fully mixed in a static mixer using metering pumps. The pressure of the tubular reactor was maintained at 1.8 MPa and the temperature was maintained at 100° C. The reaction residence time was controlled to be 90 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation, and distillation. The product yield and purity were 80% and 96%, respectively.
[0074] Embodiment 11
[0075] A method for synthesizing tert-butylaminoethoxyethanol and its derivatives based on ternary deep eutectic solvent catalysis, the specific process is as follows:
[0076] First, sodium hydroxide, ethylene glycol and choline chloride were weighed into a round-bottom flask in a molar ratio of 1:2:3, stirred at 80°C for 1 h, and then vacuum dried at 50°C for 4 h to obtain a ternary low eutectic solvent of [sodium hydroxide][ethylene glycol][choline chloride].
[0077] Subsequently, 177.35 g (3 mol) of 2-aminoethane, 152.6 g (1 mol) of 5-(2-chloroethoxy)pentanol, 6 wt% (calculated based on 5-(2-chloroethoxy)pentanol) of a ternary low eutectic solvent catalyst, and 530 g of a reaction medium methanol were added to a tubular reactor after being fully mixed in a static mixer using metering pumps. The pressure of the tubular reactor was maintained at 1.1 MPa and the temperature was maintained at 100° C. The reaction residence time was controlled to be 90 min. Finally, the reaction solution was subjected to acid-base neutralization, rough separation, and distillation. The product yield and purity were 82% and 96%, respectively.
[0078] Comparative Example 1: No ternary deep eutectic solvent added
[0079] First, 223.88 g (3 mol) of tert-butylamine, 127.1 g (1 mol) of diethylene glycol, and 530 g of reaction medium were fully mixed in a static mixer using metering pumps and then added to a tubular reactor. The pressure of the tubular reactor was maintained at 1.2 MPa and the temperature was maintained at 100° C. The reaction residence time was controlled to be 90 min. Finally, the reaction solution was subjected to acid-base neutralization, crude separation and distillation, and the product yield and purity were 75% and 96%, respectively.
[0080] From the results in the above Examples 1-10, it can be concluded that the preparation method of a ternary deep eutectic solvent provided by the present invention and the synthesis method of tert-butylaminoethoxyethanol and its derivatives catalytically synthesized in a tubular reactor can have a yield of up to 95% and a product purity of more than 98%. From Comparative Example 1, it can be concluded that under the same experimental conditions, the addition of a ternary deep eutectic solvent can significantly improve the yield of the product.
[0081] In summary, by adopting the preparation method provided by the present invention, the ternary low eutectic solvent has good catalytic performance, can significantly improve the yield of the product in the process of synthesizing tert-butylaminoethoxyethanol and its derivatives, and the process conditions such as reaction temperature, reaction pressure and reaction time are mild, which can greatly reduce the energy consumption problem in the production process of the enterprise and reduce the production cost of the enterprise.
[0082] Finally, it should be noted that the above specific implementation methods are only used to illustrate the technical solution of the present invention rather than to limit it. Although the present invention has been described in detail with reference to examples, those skilled in the art should understand that the technical solution of the present invention can be modified or replaced by equivalents without departing from the spirit and scope of the technical solution of the present invention, which should be included in the scope of the claims of the present invention.
Claims
1. A method for catalytic synthesis of tert-butylaminoethoxyethanol and its derivatives, characterized in that: Using a ternary low eutectic solvent as a catalyst, a reaction medium, a raw material represented by formula I and a raw material represented by formula II are mixed and reacted to obtain the product; The structural formula of the raw material shown in Formula I is: (I); The structural formula of the raw material shown in Formula II is: (II); Wherein, R1, R2 and R3 are independently selected from hydrogen atom, methyl, ethyl, propyl, butyl, isopropyl, hydroxyl, carboxyl, methoxy, aldehyde, hydroxymethyl, methyl substituted with 1 to 3 halogen atoms; R4 is selected from chlorine atom, bromine atom, iodine atom or aldehyde; n is 1 to 6; The preparation method of the ternary low eutectic solvent is as follows: after mixing a hydrogen bond donor and a hydrogen bond acceptor, heating at 50-120° C. for 30-200 min and then vacuum drying to obtain the ternary low eutectic solvent; The hydrogen bond donor is selected from urea and sodium hydroxide; the hydrogen bond acceptor is choline chloride; and the reaction medium is water and / or methanol.
2. The method according to claim 1, characterized in that The molar ratio of the raw material represented by formula I to the raw material represented by formula II is 2-12:
1.
3. The method according to claim 1, characterized in that: The mass ratio of the ternary low eutectic solvent to the raw material represented by formula II is 0.01-0.45:
1.
4. The method according to claim 1, characterized in that: In the raw material represented by formula I, R1 and R3 are both hydrogen atoms, and R2 is a hydrogen atom or a methyl group.
5. The method according to claim 1, characterized in that In the raw material represented by formula II, R4 is Cl, and n is 1 or 4.
6. The method according to claim 1, characterized in that The reaction temperature is 55~180℃, the pressure is 0.1~8 MPa, and the time is 30~420 min.
Citation Information
Patent Citations
Process for preparing secondary aminoether alcohols
US4487967A
Nickel-based catalyst and application of nickel-based catalyst in production of sterically-hindered amine namely tert-butylaminoethoxyethanol
CN108906061A
Preparation method of sterically hindered amine
CN116751130A
Process for producing tertiary butylamine ethoxy ethyl alcohol with space steric effect
CN1623978A